Azadirachtin - analytical standard , CAS No.11141-17-6

CAS: 11141-17-6 Cat. No.: A115081 Molecular Weight: 720.71 EC Number: 601-089-4

GRADE & PURITY Analytical standard

Synonyms

NSC 368675 | Safer BioNEEM | Suneem | Azadirachtin-A | dimethyl (2aR,3S,4S,4aR,5S,7aS,8S,10R,10aS,10bR)-10-acetoxy-3,5-dihydroxy-4-[(1aR,2S,3aS,6aS,7S,7aS)-6a-hydroxy-7a-methyl-3a,6a,7,7a-tetrahydro-2,7-methanofuro[2,3-b]oxireno[e]oxepin-1a(2H)-yl]-4-meth

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Crude extract of the neem tree. Not intended for use as a quantitative standard.

Specifications

Synonyms

NSC 368675 | Safer BioNEEM | Suneem | Azadirachtin-A | dimethyl (2aR, 3S, 4S, 4aR, 5S, 7aS, 8S, 10R, 10aS, 10bR)-10-acetoxy-3, 5-dihydroxy-4-[(1aR, 2S, 3aS, 6aS, 7S, 7aS)-6a-hydroxy-7a-methyl-3a, 6a, 7, 7a-tetrahydro-2, 7-methanofuro[2, 3-b]oxireno[e]oxepin-1a(2H)-yl]-4-meth

Specifications & Purity

analytical standard

Biochemical and Physiological Mechanisms

Triterpenoid found in need tree seeds, azadiractin suppresses feeding by many insect species and disrupts growth of most insect and other arthropod species, while having very low mammalian toxicity. Promising as a natural pesticide.

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Analytical standard

Action Type

INHIBITOR

Names and Identifiers

• Canonical Smiles: CC=C(C)C(=O)OC1CC(C2(COC3C2C14COC(C4C(C3O)(C)C56C7CC(C5(O6)C)C8(C=COC8O7)O)(C(=O)OC)O)C(=O)OC)OC(=O)C
• IUPAC Name: dimethyl (1S,4S,5R,6S,7S,8R,11S,12R,14S,15R)-12-acetyloxy-4,7-dihydroxy-6-[(1S,2S,6S,8S,9R,11S)-2-hydroxy-11-methyl-5,7,10-trioxatetracyclo[6.3.1.02,6.09,11]dodec-3-en-9-yl]-6-methyl-14-[(E)-2-methylbut-2-enoyl]oxy-3,9-dioxatetracyclo[6.6.1.01,5.011,15]pentadecane-4,11-dicarboxylate
• InChIKey: FTNJWQUOZFUQQJ-NDAWSKJSSA-N
• INCHI: 1S/C35H44O16/c1-8-15(2)24(38)49-18-12-19(48-16(3)36)32(26(39)43-6)13-46-21-22(32)31(18)14-47-34(42,27(40)44-7)25(31)29(4,23(21)37)35-20-11-17(30(35,5)51-35)33(41)9-10-45-28(33)50-20/h8-10,17-23,25,28,37,41-42H,11-14H2,1-7H3/b15-8+/t17-,18+,19-,20+,21-,22-,23-,25+,28+,29-,30+,31+,32+,33+,34+,35+/m1/s1
• Isomeric SMILES: C/C=C(\C)/C(=O)O[C@H]1C[C@H]([C@]2(CO[C@@H]3[C@@H]2[C@]14CO[C@@]([C@H]4[C@]([C@@H]3O)(C)[C@@]56[C@@H]7C[C@H]([C@@]5(O6)C)[C@]8(C=CO[C@H]8O7)O)(C(=O)OC)O)C(=O)OC)OC(=O)C
• WGK Germany: 3
• Molecular Weight: 720.71
• Reaxy-Rn: 31992430
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=31992430&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Prenol lipids
      • Subclass Triterpenoids

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Prenol lipids
• Subclass: Triterpenoids
• Intermediate Tree Nodes: Not available
• Direct Parent: Limonoids
• Alternative Parents: Tetracarboxylic acids and derivatives Furopyrans Fatty acid esters Oxepanes Oxanes Pyrans Dihydrofurans Enoate esters Tetrahydrofurans Furans Tertiary alcohols Methyl esters Cyclic alcohols and derivatives Hemiacetals Secondary alcohols Acetals Dialkyl ethers Epoxides Oxacyclic compounds Hydrocarbon derivatives Carbonyl compounds Organic oxides
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Limonoid skeleton - Tetracarboxylic acid or derivatives - Furopyran - Fatty acid ester - Oxepane - Oxane - Fatty acyl - Pyran - Cyclic alcohol - Dihydrofuran - Furan - Alpha,beta-unsaturated carboxylic ester - Tertiary alcohol - Enoate ester - Tetrahydrofuran - Methyl ester - Hemiacetal - Carboxylic acid ester - Secondary alcohol - Dialkyl ether - Acetal - Carboxylic acid derivative - Ether - Oxirane - Organoheterocyclic compound - Oxacycle - Organooxygen compound - Alcohol - Carbonyl group - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Aliphatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17.
• External Descriptors: Apotirucallane triterpenoids

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

NR1H4 Tclin Bile acid receptor FXR (6228 Activities)

Discover Target: NR1H4

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Spodoptera littoralis (798 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Bemisia tabaci (599 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Spodoptera litura (1708 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Nfe2l2 Nuclear factor erythroid 2-related factor 2 (214 Activities)

Discover Target: Nfe2l2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Helicoverpa armigera (708 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Nr1i2 Nuclear receptor subfamily 1 group I member 2 (14 Activities)

Discover Target: Nr1i2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Olepa ricini (40 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Henosepilachna vigintioctopunctata (143 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Melt Point(°C): 165℃
• Molecular Weight: 720.700 g/mol
• XLogP3: -0.600
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 16
• Rotatable Bond Count: 10
• Exact Mass: 720.263 Da
• Monoisotopic Mass: 720.263 Da
• Topological Polar Surface Area: 215.000 Ų
• Heavy Atom Count: 51
• Formal Charge: 0
• Complexity: 1660.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 16
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1

References

1. Benshui Shu, Yanzheng Lin, Guozhao Qian, Xueming Cai, Luyang Liu, Jintian Lin.  (2022)  Integrated miRNA and transcriptome profiling to explore the molecular mechanism of Spodoptera frugiperda larval midgut in response to azadirachtin exposure.  PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY,      [PMID:36127051] [10.1016/j.pestbp.2022.105192]

2. Yu Haikuo, Yang Xianmei, Dai Jinghua, Li Yuning, Veeran Sethuraman, Lin Jintian, Shu Benshui.  (2022)  Effects of azadirachtin on detoxification-related gene expression in the fat bodies of the fall armyworm, Spodoptera frugiperda.  ENVIRONMENTAL SCIENCE AND POLLUTION RESEARCH,  30  (15): (42587-42595).  [PMID:35294689] [10.1007/s11356-022-19661-6]

3. Hai-bo Wu, Peng-xin Guo, Lin-hui Ma, Xi-meng Li, Ting-ting Liu.  (2021)  Nematicidal, antifungal and insecticidal activities of Artemisia halodendron extracts: New polyacetylenes involved.  INDUSTRIAL CROPS AND PRODUCTS,      [PMID:] [10.1016/j.indcrop.2021.113825]

4. Benshui Shu, Haikuo Yu, Yuning Li, Hongxin Zhong, Xiangli Li, Liang Cao, Jintian Lin.  (2020)  Identification of azadirachtin responsive genes in Spodoptera frugiperda larvae based on RNA-seq.  PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY,      [PMID:33518039] [10.1016/j.pestbp.2020.104745]

5. Wen-kui Li, Song Wang, Yong-hong Wang, Yu-zhen Wu, Jia Li, Tian-hua Chai, Kang Wang, GuangYou Chen, Zhiqing Ma.  (2025)  Nanoporous 3D Polyurethane for Toosendanin Adsorption, Encapsulation, and High-Efficient Utilization.  JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,      [PMID:39932266] [10.1021/acs.jafc.4c09493]

6. Benshui Shu, Yuting Huang, Xinyi Xie, Cuiting Liu, Jintian Lin, Ying Xiao, Jingjing Zhang.  (2025)  Functional analysis of Sf-NPF1 in food intake and antifeedant induction by azadirachtin in Spodoptera frugiperda larvae.  PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY,      [PMID:40915827] [10.1016/j.pestbp.2025.106567]

7. Yubing Ma, Huiying Yan, Omar S. Abukhader, Daiqin Li, Shichang Zhang.  (2025)  Sublethal effects of matrine and azadirachtin on the wolf spider Pardosa laura: no impairment of growth but marked suppression of reproduction.  PEST MANAGEMENT SCIENCE,      [PMID:41208300] [10.1002/ps.70347]